We have a 19' ft trailer-sailor and still love her to bits. Easy to tow anywhere, and it's mainly in a slip a 10 min walk from the house
Luxury.
26 to 21 ft is a big jump down in terms of
interior size and livability. So if the bulk of your sailing involves overnighting, cruising and/or lots of people... it's not a great move. On the other hand, if like us you daysail 90% of the time, and just do the odd weekend out, a smaller boat might be tolerable.
Looking at pictures of a San Juan 26... If it was me I'd keep her, no question.
Here's a thought - store the San Juan at the coast, either in the
water or on land close to a good
ramp. You'd save the wear and expense of the long tow. For sailing closer to home, you might consider
buying another
cheap daysailor or mini cruiser, which, if you're handy, can be picked up for
cheap.
We push our 19' boat with an older 5HP Suzuki and it's plenty strong enough, even in
current or against
wind. So a 9.8 hp
outboard is a little bit overkill and heavy for a 21' boat, I think.